I'm pretty sure that succeeding in this is not going to be a matter of how many "stars" your project has, but rather a function of the dollar value of the problem your software solves and how well you market the paid product. You should start that marketing now by providing a link to your project :).
If you're interested, I recommend listening to his interviews on the ChangeLog Podcast (https://changelog.com/159/, https://changelog.com/130/, https://changelog.com/92/) where he talks about how he monetised those products.
I'm pretty sure that succeeding in this is not going to be a matter of how many "stars" your project has, but rather a function of the dollar value of the problem your software solves and how well you market the paid product. You should start that marketing now by providing a link to your project :).